109 Jackson St · Winchester, KY 40391

$90,000

2 bd · 1.0 ba · 1,218 sqft · Other · 20 Days on market

Built 1940

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Why this score? — see what drove the B- grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• Cash flow +30.0/30.0
• DSCR +10.0/10.0
• 1% rule +8.7/10.0
• ARV discount +7.5/15.0
• Schools +3.0/10.0
• Livability +3.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Convenient location to downtown Winchester! Home to be sold as is.

Key facts

• Built 1940
• Listed 20 days

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath other listed at $90k.

Deal economics

• At list price, monthly cash flow is $432 ($5k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($1k rent vs $90k).
• Recommended offer: $89k (1.5% below list) — sets the bar for market timing.
• Cap rate 12.1% vs local median 4.0% in Winchester — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

• Location reads 60/100 on livability (#393 in KY) — a middle-class / working-renter tenant base. Strengths: cost of living A+, housing A+; Watch: schools D+, amenities F, commute F.
• Clark County (town): math 28% / reading 41% proficiency, ranked #64 of 165 in KY (top 39%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Market conditions: 291 active listings in the ZIP; 8 comparable units currently listed for rent nearby; rentals at typical pace (median 21d on market — plan ~3-4 weeks tenant-placement turnaround); 160 units permitted in Clark County in 2024 (61 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $622 of loan paydown is wiped out by about $3k of value loss. Plan a longer hold.
• Clark County population projected to shrink 7% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $25k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• It's been on market 20 days — a 2% lower offer ($89k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 13y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
• Current owner paid $14k; list at $90k implies a 567% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1940 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $88,650 (1.5% below list)

Questions for the listing agent

1. Built in 1940 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
4. What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
5. What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
6. How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 1.37% ✓
• Cap rate: 12.06%
• Cash-on-cash: 20.58%
• DSCR: 1.92
• GRM: 6.1

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 12.9%
• Equity multiple: 1.51×
• Total profit: $12,917
• Equity at exit: $13,419

10-year hold

• IRR: 21.7%
• Equity multiple: 2.85×
• Total profit: $46,576
• Equity at exit: $7,782

Cash invested: $25,200 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 83 Strongly Landlord-Friendly
• State Kentucky: 83 Strongly Landlord-Friendly · R+16
• County: — inherits STATE
• City: — inherits STATE

7-day pay-or-quit (URLTA cities); generally landlord-friendly.

Methodology + full state rankings →

ZIP-level market 40391

• Home prices YoY: -17.0%
• Active inventory: 291
• Price-to-rent: 6.1×

Monthly cashflow live

• Estimated rent: $1,234 high
• Mortgage (P&I): −$472
• Tax from tax record: −$33 /mo · $394/yr
• Insurance: −$38
• HOA: −$0
• Vacancy / Maint / Mgmt: −$259
• Net cashflow: $432

Break-even live

Break-even rent $686

Max offer price $90,000

Occupancy floor 60%

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $22,500
• Closing costs: $2,700
• Reserves months: —
• Total cash needed: —

Rent comps 8 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
18 Calloway St Winchester, KY	1.0	1.0	850	$879	$1.03	21d	1	0.52mi
204 S Maple St Winchester, KY	2.0	1.0	1400	$1,395	$1.00	13d	1	0.64mi
502 Evans St Unit 3 Winchester, KY	3.0	1.0	1200	$1,400	$1.17	23d	1	0.87mi
362 S Main St Unit A Winchester, KY	1.0	1.0	996	$996	$1.00	23d	1	0.88mi
25 Hays St Winchester, KY	2.0	2.0	1250	$1,300	$1.04	23d	1	1.02mi
1071 Two Mile Rd Winchester, KY	2.0	2.5	1100	$1,299	$1.18	13d	1	1.21mi
403 Atrium Pl Winchester, KY	2.0	1.5	960	$975	$1.02	13d	1	1.22mi
100 Sam Winston Way Winchester, KY	2.0	2.5	1100	$1,499	$1.36	13d	1	1.29mi

Listing history 17 events

1. 2026-06-18
   days on market $90,000 Active 20 DOM
2. 2026-06-17
   days on market $90,000 Active 19 DOM
3. 2026-06-16
   days on market $90,000 Active 18 DOM
4. 2026-06-15
   days on market $90,000 Active 17 DOM
5. 2026-06-14
   days on market $90,000 Active 15 DOM
6. 2026-06-13
   days on market $90,000 Active 14 DOM
7. 2026-06-10
   days on market $90,000 Active 12 DOM
8. 2026-06-09
   days on market $90,000 Active 11 DOM
9. 2026-06-08
   days on market $90,000 Active 10 DOM
10. 2026-06-07
    days on market $90,000 Active 9 DOM
11. 2026-06-05
    days on market $90,000 Active 6 DOM
12. 2026-06-03
    days on market $90,000 Active 5 DOM
13. 2026-06-02
    days on market $90,000 Active 4 DOM
14. 2026-06-01
    days on market $90,000 Active 3 DOM
15. 2026-05-31
    days on market $90,000 Active 2 DOM
16. 2026-05-31
    remarks 66-char remark
17. 2026-05-31
    listed $90,000 Active 1 DOM

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast KY · Resets to sale price

• Current annual tax: $394 · $33/mo
• Projected year-2 tax: $774 · $64/mo
• Expected delta: +$380/yr (+$32/mo · 96.4%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥101°F today · 19 d/yr by 30 yrs out
• 💨 Wind 2/10 Low 3% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 0 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $14,804
• − Mortgage interest: −$5,041
• − Property taxes: −$394
• − Insurance: −$450
• − Repairs & maintenance: −$1,184
• − Management: −$1,184
• − Depreciation: −$2,618
• Taxable income: $3,932
• Est. tax owed @ 24.0%: −$944
• After-tax cash flow: $4,244/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

• District: Clark County
• NCES district ID: 2101200
• Math proficiency: 28% ▼ -25.00%
• Reading proficiency: 41% ▼ -18.00%
• Median HH income: $47,282
• Composite: 29.63/100
• National rank: #6469
• State rank: #64 of 165 in KY

Livability — Winchester

• Score: 60/100
• State rank: #393
• US rank: #18931

Category grades

Amenities F Commute F Cost of living A+ Crime C+ Employment F Housing A+ Health & safety F User ratings F

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Winchester, KY
• County: Clark County · 36,796 people
• City population: 36,796
• Metro: Lexington-Fayette, KY
• Population (ZIP): 36,796
• Household income: $64,144
• Rent vs Own: 29.4% rent · 70.6% own
• Severe rent burden: 854.0

Population outlook (Clark County) Hauer SSP2

• Today (2025): 35,849 people
• By 2030: 35,616 · -0.6%
• By 2040: 34,727 · -3.1%
• By 2050: 33,195 · -7.4%
• By 2075: 29,439 · -17.9%
• By 2100: 24,744 · -31.0%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (88%)
• Race & ethnicity: White 88% Black 4% Hispanic / Latino 4% Two or more races 3%
• Common ancestry: Slovak 3% Italian 2% Serbian 2%
• Foreign-born: 2% · Canada
• Languages at home: 97% English-only · Spanish 2%

Political lean MEDSL · Clark

• 2024 margin: Solid R (+35.3) · D 31.6% · R 66.9% · Other 1.6%
• 2008→2024 swing: -10.3pp toward R · 2008: -25.1pp · 2024: -35.3pp
• All cycles: 2024: R+35.3 2020: R+32.0 2016: R+37.1 2012: R+30.5 2008: R+25.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -58.24%
• Current HPI: 283.7839
• Rent YoY: —
• Metro: Lexington-Fayette, KY
• State GDP YoY: ▲ 1.81%
• F500 in state: 4

Industry mix (Fortune 500 HQ in KY)

Industry	F500 HQs	Revenue
▸Healthcare	1	$118B
▸Food / Beverage	1	$7B

Price history

+566.7% since first listed

4 events — show timeline

• 2026-05-30 Listed $90,000 FSBO.com
• 2014-06-05 Listing Removed — ImagineMLS
• 2013-07-26 Listed $45,000 ImagineMLS
• 1977-03-01 Sold (Public Records) $13,500 Public Records

Property tax history

+1.6%/yr

Latest (2025): $394 · +9.7% YoY. Source: county tax records.